期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 30, 页码 10886-10889出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja405547f
关键词
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资金
- National Institutes of Health [GM 25439]
- Robert A. Welch Foundation [F-0652]
The first enantioselective total synthesis of (-)-citrinadin A has been accomplished in 20 steps from commercially available materials via an approach that minimizes refunctionalization and protection/deprotection operations. The cornerstone of this synthesis features an asymmetric vinylogous Mannich addition of a dienolate to a chiral pyridinium salt to set the initial chiral center. A sequence of substrate-controlled reactions, including a highly stereoselective epoxidation/ring-opening sequence and an oxidative rearrangement of an indole to furnish a spirocodndole, are then used to establish the remaining stereocenters in the pentacyclic core of (-)-citrinadin A. The successful synthesis of citrinadin A led to a revision of the stereochemical structure of the core substructure of the citrinadins.
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